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Originally from Jamaica, Sleepy Hallow grew up in Flatbush, Brooklyn getting into trouble as a juvenile. Although as a kid he always did well in school. In 2018 he had his first breakthrough viral single with "Flows,” which also featured Sheff G. In August 2020, his single "Deep End Freestyle '' featuring Fousheé was certified platinum by the RIAA. More recently, Sleepy’s single "2055" peaked at number 53 on the Billboard Hot 100 Chart, becoming his highest-charting song thus far. He is currently signed to Winners Circle Entertainment and RCA Records. In 2021, he was selected as a HipHopDX Rising Star.
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Sleepy Hallow is from Jamaica. He moved to America when he was in grade school.
Yes. According to Sheff G, originally him and his friends planned to jump Sleepy Hallow after school when they were kids. However, he liked the way Sleepy Hallow stood up for himself and they became friends afterwards. The two both signed to the same record label, RCA in 2020 and are frequent collaborators. In 2021, Sleepy Hallow was selected as a HipHopDX Rising Star.
According to Audible Treats, Sleepy Hallow’s name plays on the headless horseman in the gothic literature “Sleepy Hollow,” which comes from his own haunting world on the block in Brooklyn.
Sleepy Hallow is 21 years old. He will be 22 on December 20, 2021.
Sleepy Hallow has one daughter named Melina.
Sleepy Hallow made his name with the iconic "Panic" set of singles. He helped push the Brooklyn-drill genre forward alongside close collaborator Sheff G. He became mainstream and had chart success with his 2020 single "Deep End Freestyle."
Real name: Tegan Joshua Anthony Chambers
Aliases:
Sheff G & Sleepy Hallow Are Ready To 'Run It Up'
Videos | Aug 18, 2021, 11:56 AM PDT
Sleepy Hallow Doesn't Quite Wake Up His Detractors On 'Still Sleep?'
Reviews | Aug 5, 2021, 3:05 PM PDT
Toosii Drops Deluxe Album 'Thank You For Believing: The Manifestation' + 42 Dugg Posts Questionable Video
Editorials | Aug 1, 2021, 10:11 AM PDT
Coi Leray Joins Sleepy Hallow For New Version Of ‘2055’
News | Jul 30, 2021, 10:21 PM PDT
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Yung Bleu Announces Debut Album 'Moon Boy' & Drops Heavy-Hitter Infused Tracklist
Editorials | Jul 18, 2021, 11:52 AM PDT
Sheff G & Sleepy Hallow's Rap Originality Praised After Huge Festival Look
News | Jul 17, 2021, 1:56 PM PDT
42 Dugg Joins Tyler The Creator on 'Lemonhead' As Sheff G Heads To Summer Jam
Editorials | Jun 27, 2021, 11:00 AM PDT
Sleepy Hallow Drops 'Still Sleep? As Morray Goes Gold & Yung Bleu Catches Lawsuit
Editorials | Jun 6, 2021, 5:00 PM PDT
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New Music Friday - New Albums From Lil Baby + Lil Durk, Lloyd Banks, Sleepy Hallow + More
News | Jun 3, 2021, 9:36 PM PDT
HipHopDX Rising Star Sleepy Hallow Shares ‘Still Sleep?’ Album
News | Jun 2, 2021, 9:15 AM PDT